The Bet
by Athena Wonderland
Summary: AU! Based off of a painting I saw on pinterest. Dean and Sam make a bet that if Sam can propose to Jess within a week, Dean will confess his true feelings to Castiel


Disclaimer: I don't own anything except 8 seasons of _Supernatural_ and a piece of pie… that is, until I ate the pie.

I haven't written any stories in a while (like a couple of years), BUT my mom, sister, and I have decided to take a summer writing challenge where we try to write at least one story a week. My sister and I are drawing a pairing and a prompt out of a hat each week.

This Week: "Destiel" and "Based off of a Painting"

Story is based off this painting:

http themetapicture com one-of-the-most-amazing-oil-paintings-by-artist-leonid-afremov

Dean sat on the bench. His dog, Crowley, sat at his feet and gave a small growl and a glare. Dean gave him a look back. Crowley turned around and looked at the ground. Dean sighed. Then it began to rain.

"Dammit," he said aloud to nobody in general. "No one said anything about any stupid rain tonight," he grumbled. He leaned forward and put his face in his hand.

"_**Carry on my wayward son! There'll be peace when you are done! Lay yo-**_**"**

"What is it Sammy?" Dean grumbled as he answered his phone.

The voice in the receiver gave a sigh, "You're never going to stop calling me that are you?"

"Nope. Now what is it?"

"You kind of ran out of the house without an explanation. What happened between you and Cas? He seems kind of worried and freaked out," Sam questioned.

"Just needed to take Crowley for a walk. You know how it is," Dean responded, ignoring the last part of the question.

"And what about Cas?"

"Nothing, Sammy! Don't worry about it!"

"Would this have anything to do with the vow that you would never have a chick flick moment between anyone?"

"Actually, yes. Yes, it does. And for that same reason, I'm going to hang up now," Dean said, ending the call between him and his brother, before Sam could get out another word. He stuffed the phone back into his pocket. He then gave another sigh and thought back to earlier that evening.

*FLASHBACK TIME*

_Castiel sat on the couch, confused._

"_Dean, why did you bring me here? The others have gathered in kitchen area," Castiel asked. Sam had invited everyone over to celebrate his and his girlfriend Jess' engagement. Sam and Dean had also made a bet. If Sam proposed within a week of them making the bet, then Dean would tell Castiel, who Dean had been in love with for about 2 years, 3 weeks, and 4 days (and an hour and 20 minutes give or take), that Dean liked him. Dean (OBVIOUSLY) thought that Sam would lose his nerve and wouldn't propose. Well, that's how he got here, having to confess to his crush, with his little brother gloating in the kitchen and Jess, as sweet as she was, giving him looks that practically screamed 'GET THE HELL ON WITH IT!'._

"_Castiel-"_

"_Oh no. When you use my full name there's always something wrong," Castiel began to freak out._

"_No! Cas! It's-"_

"_Is this because of me saying that getting Crowley was a bad idea because he reminded me of a demon?"_

"_No-"_

"_Or because I took your AC-DC records and didn't give them back?"_

"_No, but-"_

"_Or is this because I stole your Kansas t-shirt?"_

"_No, it's- Wait. You took my Kansas shirt!?" Dean said shocked. Cas gave a sheepish look._

"_Maybe." Cas looked down and began to wring is hands. Dean sat down next him and stopped him._

"_Cas. I'm not mad about the shirt. But I still need to talk to you about something," Dean held Cas' hands. Castiel looked down and sucked in a breath._

"_Yes, Dean?"_

"_I, ah, I really," Dean began to stutter, "I like you, Castiel."_

"_I like you too, Dean," Cas said, confused, "You're my best friend."_

_Dean turned in to face Castiel more, "No, I mean I like you as more than a friend. Like in a romantic sort of way." Dean leaned in to Castiel's face and gave him a gentle kiss on the lips. He pulled back and looked at Cas' face for some sign he felt the same._

"_Hey guys, come on. The party's in-" Sam started as he entered into the living room area, startling the occupants, "Are you guys in the middle of something, or - ?"_

"_No. Not at all. I was just leaving," Dean said automatically standing up and heading to the door._

"_Dean-" Castiel began quietly._

"_I'll see you later, Castiel," Dean said, and he began to head home._

*ENDING OF THE FLASHBACK*

Dean rubbed his face and leaned back. Crowley tugged on his leash. He stood up and gave a grunt. He nudged Dean's knee. Dean looked at him.

"What is your problem, Crowley?" Dean muttered.

"I guess he just wanted to inform you I was here," said a familiar voice. Dean's head went up so fast, he almost got whiplash.

"Cas," he said, shocked. He got up from the bench. Cas stood a couple of feet away in his trench coat.

"You left before I could say anything to you about what had happened," Cas said, staring Dean down.

"Well, there's not much to say now is there?" Dean said, staring back.

"There is a lot to say, Dean," Cas shot back at him, "For example, do you know how long I have waited to hear you say that? Do you realize how long I've been in love with you? I do. About 3 years almost to date."

Dean stared in shock, "We met three years ago, Cas."

Cas looked down. "I know. It was practically love at first sight. And when you told me how you felt tonight, I was in shock. I was so, so happy, Dean. I just-" Cas was cut off by a pair of lips. The two kissed as the rain came down. They split apart.

"Wow," they said at the same time, and kissed again. The rain continued to fall on them.

"Do you want to come back to my place?" Dean asked.

"Sure," Cas said giving Dean one more kiss. Dean picked up Crowley's leash, wrapped his arm around Castiel's waist, and the three of them headed home. Wait till Sam heard this story. So worth the bet.

Hope you all enjoyed! Please review!


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